CN106810622A - It is a kind of that neohesperidin and the method to dried immature fruit of citron orange comprehensive utilization are extracted from the dried immature fruit of citron orange - Google Patents
It is a kind of that neohesperidin and the method to dried immature fruit of citron orange comprehensive utilization are extracted from the dried immature fruit of citron orange Download PDFInfo
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Abstract
Neohesperidin and the method to dried immature fruit of citron orange comprehensive utilization are extracted from the dried immature fruit of citron orange the invention provides a kind of.The method of the comprehensive utilization includes：1) dried immature fruit of citron orange is crushed, is sieved；2) temperature in use is that 55 60 DEG C of water is extracted to the material after sieving, and leaching liquor and filter residue are collected respectively；3) filter residue purify obtaining aurantiamarin；And/or, the leaching liquor is separated, obtain one or more in jelly powder, aurantiin, neohesperidin.The method that the present invention is provided has maximally utilised the dried immature fruit of citron orange, and the method for the present invention is mainly extracted with warm water, and follow-up a small amount of alcohol is isolated and purified, and the use of organic solvent is reduced to greatest extent, and process is simple effectively, is with a wide range of applications.
Description
Technical field
Field is isolated and purified the present invention relates to Effective Component of Chinese Medicine, extracts new from the dried immature fruit of citron orange more particularly, to one kind
Aurantiamarin and the method to dried immature fruit of citron orange comprehensive utilization.
Background technology
The dried immature fruit of citron orange is the young fruit that dries of Rutaceae Citrus bitter orange or sweet orange mutation, and bitter, property are pungent cold, with relieving stagnant Qi, disappear
Product, effect of resolving sputum, can treat internal stagnation, constipation, rush down dysentery, feeling of fullness abdominal distension, accumulation of pathogens in chest, prolapse of the anus, effect of gastroptosis.
Hesperidine in modern medicine study Bitter Orang P.E has the effect to cardiovascular system blood pressure control, pungent in Bitter Orang P.E
Fu Lin has the effect for increasing gastrointestinal motility, and the dried immature fruit of citron orange flavones in Bitter Orang P.E has anti-haemocyte cohesion, antithrombotic in addition
The effects such as formation, anticancer, antimycotic, anti-inflammatory.
The dried immature fruit of citron orange contains 10-15% pectin, 7-8% aurantiins, 1% or so aurantiamarin, 8% or so neohesperidin, total yellow
Ketone content 25% or so, other important components Xin Folin, river hesperetin, Quercetin, rutin, D- limonenes (the Chinese medicine group of essential oil
Into), lutein, zeaxanthin etc., these materials all have obvious health-care efficacy and medical effect, thus the dried immature fruit of citron orange have it is good
Good comprehensive utilization value.
But current neohesperidin is cheap, and raw material and extraction cost are high, and manufacturer depends merely on one to lose more than gain, and
And the waste and pollution of resource are also resulted in, while at present to other active ingredients such as jelly powder, aurantiin, aurantiamarin in the dried immature fruit of citron orange
The report for efficiently separating and purifying is little.
The content of the invention
Regarding to the issue above, the invention provides a kind of method, the dried immature fruit of citron orange is make use of to greatest extent, isolate to greatest extent
Active ingredient such as neohesperidin, jelly powder, aurantiin and/or aurantiamarin in the dried immature fruit of citron orange, not only the creation of value but also had reduced environmental pollution.
The invention provides a kind of method to dried immature fruit of citron orange comprehensive utilization, methods described includes：
1) dried immature fruit of citron orange is crushed, is sieved；
2) temperature in use is extracted for 55-60 DEG C of water to the material after sieving, and leaching liquor and filter residue are collected respectively；
3) filter residue purify obtaining aurantiamarin；And/or, the leaching liquor is separated, obtain jelly powder,
One or more in aurantiin, neohesperidin.
Preferably, step 1) it is described sieving be 14 mesh sieves.
Preferably, the step 2) in extracting times be 2-3 times, total consumption of the water is preferably raw material survival dose
12-16 times.
Preferably, the time of the extraction is 4-6 hours.
More preferably step 2) in extracting times be 2 times：The consumption of extraction water is 8-10 times of bulk drug, second for the first time
The consumption for extracting water is 4-6 times of bulk drug.
Preferably, the method for purification of the aurantiamarin is as follows：
Filter residue saturated limewater is dissolved, supernatant is taken and is adjusted to acidity, cooling takes precipitation, removal of impurities is done
Aurantiamarin is obtained after dry.
Preferably, the removal of impurities includes dissolving precipitation alkali lye, and filtrate is adjusted into acidity, cool overnight after filtering
After obtain final product；More preferably by the alkali lye dissolving that the precipitation pH value is 10-12, filtrate is adjusted to pH value for 2-5 after filtering.
Most preferably by the alkali lye dissolving that the precipitation pH value is 11, it is 4 that filtrate is adjusted into pH value after filtering.
Preferably, the separation of jelly powder comprises the following steps：
The leaching liquor is concentrated in vacuo, alcohol precipitation, separating filtrate and sediment is carried out in the case where temperature is not less than 55 DEG C,
By the sediment water dissolves, decolourize, filtering, spray drying obtains final product jelly powder.
Preferably, vacuum is -0.08--0.09MPA in the vacuum concentration, and temperature is 55-60 DEG C, the proportion of concentration
It is not less than 1.15.
Preferably, alcohol is not less than 80% alcohol for concentration in the alcohol precipitation, the consumption of alcohol for 5 times of concentrated extract and
More than.
Preferably, the temperature of the alcohol precipitation is 55 DEG C -65 DEG C, more preferably 65 DEG C.
Preferably, the separation method of the aurantiin and/or neohesperidin is as follows：
The filtrate is concentrated in vacuo, water-filling is entered in the case where temperature is not less than 70 DEG C and is sunk, supernatant is taken after centrifugation, cooled down
Obtain the sediment containing aurantiin and neohesperidin；
To the alcohol for adding temperature to be not higher than 5 DEG C in the sediment containing aurantiin and neohesperidin, obtained after centrifugation
Clear liquid and thick neohesperidin sediment, will obtain aurantiin after supernatant concentration.
Preferably, the separation method of the neohesperidin is as follows：
To alkaline solution is added in the thick neohesperidin sediment, it is sufficiently mixed, filtrate is taken after filtering, then filtrate is adjusted
To acid, collect and precipitate and recrystallize, obtain neohesperidin.
Preferably, vacuum is -0.08--0.09MPA in the vacuum concentration, and temperature is 55-60 DEG C, the proportion of concentration
It is not less than 1.15.
Preferably, the heavy temperature of preferably described water is 70-80 DEG C.
Preferably, the temperature of preferably described alcohol is 0-5 DEG C, and the concentration of alcohol is not less than 80%.
Preferably, the pH value of alkaline solution is 10-12, and the pH value of acid filtrate is 2-5.
It is highly preferred that the pH value of alkaline solution is 11, the pH value of acid filtrate is 4.
Preferably, the solvent of recrystallization is not less than 80% ethanol for concentration, and the temperature of ethanol is not less than 60 DEG C.
Another aspect of the present invention, additionally provides a kind of method that neohesperidin is extracted from the dried immature fruit of citron orange, methods described bag
Include：
The dried immature fruit of citron orange is crushed, is sieved；
Temperature in use is extracted for 55-60 DEG C of water to the material after sieving, and leaching liquor and filter residue are collected respectively；
The leaching liquor is concentrated in vacuo, alcohol precipitation, separating filtrate and sediment are carried out in the case where temperature is not less than 55 DEG C；
The filtrate is concentrated in vacuo, water-filling is entered in the case where temperature is not less than 70 DEG C and is sunk, supernatant is taken after centrifugation, cooled down
Obtain the sediment containing aurantiin and neohesperidin；
It is 0-5 DEG C of alcohol to temperature is added in the sediment containing aurantiin and neohesperidin, supernatant is obtained after centrifugation
Liquid and thick neohesperidin sediment；
To alkaline solution is added in the thick neohesperidin sediment, it is sufficiently mixed, filtrate is taken after filtering, then filtrate is adjusted
To acid, collect and precipitate and recrystallize, obtain neohesperidin.
The method that the application is proposed, with advantages below：
1) raw material that is used in the inventive method, equipment is common common raw material, equipment, it is to avoid industrialized production
During for expensive raw materials, the dependence of equipment, greatly reduce production cost, the method for the present invention is utilized to greatest extent
The dried immature fruit of citron orange, isolates active ingredient such as neohesperidin, jelly powder, aurantiin and/or the aurantiamarin in the dried immature fruit of citron orange to greatest extent.
2) main using warm water extraction in the present invention, temperature control greatly reduces macromolecular water solubility miscellaneous in 55-60 degree
The extraction of matter, greatly improves the purity of each material, reduces purification step, greatly make use of the dried immature fruit of citron orange.
3) all using common extraction, concentration, drying equipment, invest low, simple to operate low to workman's technical requirements, do not have
Macroreticular resin etc. does investment extraction purification equipment, effectively prevents the pollution to environment such as macromolecular resin.
3) only using most common edible alcohol as the organic solvent for isolating and purifying during, environmental pollution is little,
Non-toxic, low cost, reclaims easy.
4) what the present invention took is a kind of technology path of environmental protection economy, and the extraction used in the technology path is dense
The production equipments such as contracting, purifying can use closed system, during operation, can to greatest extent avoid operating personnel from contacting
To reagent, the health of human body has effectively been ensured.The solvent used in the method, waiting to recycle, and can reduce material damage
Lose, improve product yield.The technology path is mutually echoed in the pattern of China's sustainable development, there is good social benefit.
Specific embodiment
With reference to embodiment, specific embodiment of the invention is described in further detail.Following examples are used for
The present invention is illustrated, but is not limited to the scope of the present invention.
The invention provides a kind of method to dried immature fruit of citron orange comprehensive utilization, the method includes：
1) dried immature fruit of citron orange is crushed, is sieved.
Treat treated substance to be selected, remove what silt rotted to go mouldy etc., it is necessary to which the dried immature fruit of citron orange too high to moisture content is carried out
Drying, then disintegrating machine is crushed to the dried immature fruit of citron orange.
In order to further improve purity and the rate of recovery, it is preferable that it is required that broken pulverized powder crosses 14 mesh sieves completely.Powder is too thin
Easily hardened after extraction, impurity is more into extract solution, the difficulty that increase is isolated and purified, and the purity of object reduces；Powder is excessively thick,
Extraction time can extend, and impurity is easily accessible in extract solution, extract relatively not enough fully, reduce the rate of recovery.14 mesh are being crossed completely
The powder of sieve, can obtain purity object higher, and the rate of recovery is also higher.
2) dried immature fruit of citron orange after sieving is extracted using water, leaching liquor and filter residue is collected respectively；Wherein, the temperature of water is
55-60 DEG C, greatly reduce the extraction of macromolecular water-solubility impurity.
In the present invention, when extraction temperature is higher than 60 degree, aurantiamarin largely enters in leaching liquor, easily causes new orange peel
The separation of glycosides and aurantiamarin is difficult, and temperature three kinds of materials higher are more easily dissolved in leaching liquor, when extraction temperature is higher than 70 degree
When, aurantiamarin, neohesperidin and aurantiin largely can be dissolved in leaching liquor, be difficult to separate；In addition, the too low aurantiamarin of temperature,
Neohesperidin and aurantiin can not be all dissolved in leaching liquor, and the temperature lower time for needing to extract is more long, it is difficult to three is divided
Open, the temperature control of leaching liquor at 55-60 DEG C, can be realized separating three, and lose less by the present invention well.
In order to further improve the dissolution rate of target separator, the step 2) in extraction be Ultrasonic Wave-Assisted Extraction,
Further increase extracting effect.
It is demonstrated experimentally that the dissolution rate that can make target separator using ultrasonic-leaching improves 15-20% or so.
From the point of view of cost angle and extracting effect, the extracting times are preferably 2-3 times.
The extraction time is preferably 4-6 hours.
Total consumption of the water is preferably 12-16 times of raw material survival dose.In order that effective component yield is high, step 2) in
Extracting times are more preferably 2 times：
The consumption of extraction water is more preferably 8-10 times of bulk drug for the first time, most preferably 10 times, water is extracted for the second time
Consumption is more preferably 4-6 times of bulk drug, most preferably 5 times.Can as far as possible will be new in Immature Orange Fruit in the amount ranges
Aurantiamarin, aurantiin, pectin dissolved well out, and do not increase the energy consumption cost that subsequent technique is concentrated, and water is very few can not be abundant
Extract, influence organic efficiency, dilutional hyponatremia increases facility load, increases subsequent concentration energy consumption.
Wherein, in the present invention, the consumption of water refers to volume, and bulk drug refers to gravimetric value.
Wherein, ultrasound can not be used in second extraction, merges secondary raffinate and collect filter residue.
In order to be able to preferably utilize the dried immature fruit of citron orange, 3) method of the present invention comprises the following steps：
2) filter residue described in purify obtaining aurantiamarin；And/or, the leaching liquor is separated, obtain pectin
One or more in powder, aurantiin, neohesperidin.
The method of purification of the aurantiamarin is as follows：
2) saturated limewater of filter residue described in is dissolved, supernatant is taken and is adjusted to acidity, cooling takes precipitation, removes
It is miscellaneous, can obtain aurantiamarin after drying.
Wherein, saturated limewater neutral and alkali calcium ion can be combined with some tannin protein-polysaccharides and produce precipitation, while
It is alkaline gentle, the stabilization of flavone compound can be maintained under compared with elongate member.In this step, dissolved using saturated limewater
Filter residue can play dissolution, may also function as removal of impurities effect so that removal of impurities is more abundant, and the aurantiamarin for obtaining is purer.
In order to allow aurantiamarin sufficiently to separate out, the pH value of acid solution is preferably 2-5, more preferably 4.
Wherein, removal of impurities can use impurity-removing method common in this area.In order to reduce the introducing of impurity as far as possible with
And the effect of removal of impurities is improved, removal of impurities preferably uses the heavy method of alkali soluble acid.Preferably, in pH in the alkaline solution of 10-12
Fully dissolving, obtains filtrate after filtering, filtrate obtains sediment with cool overnight in acid solution regulation pH to 2-5, centrifugation.
Wherein, the pH value of alkaline solution is more preferably 11, and the pH value of acid solution is more preferably 4.Wherein, alkaline solution is excellent
Elect the most frequently used sodium hydroxide solution in this area as.Acid solution is preferably the most frequently used hydrochloric acid solution in this area.
By above-mentioned precipitate washed with water, dry 98.2%-98.5% aurantiamarin white, needle-shaped crystals.
The separation method of the jelly powder, aurantiin and neohesperidin is as follows：
2) leaching liquor described in is further separated, the one kind in jelly powder, aurantiin, neohesperidin can be obtained
Or it is various, so as to greatest extent and effectively using the dried immature fruit of citron orange.
Wherein, the separation method of the jelly powder is as follows：
The leaching liquor is concentrated in vacuo, alcohol precipitation, separating filtrate and sediment is carried out in the case where temperature is not less than 55 DEG C,
By the sediment water dissolves, decolourize, filtering, spray drying obtains final product jelly powder.
Wherein, in order to shorten concentration time, active component will not be inactivated under lower temperature or lost activity on a small quantity,
Concentration is preferably and is concentrated in vacuo, and vacuum is preferably -0.08--0.09MPA.Meanwhile, in order to reduce the mass expansion after concentration,
Temperature is preferably 55-60 DEG C in concentration process.
Wherein, in order to reduce energy consumption, the medicinal extract generally after concentration is more than 1.15, more preferably 1.15-1.20.In this hair
In bright, extract medicinal extract proportion be 1.15-1.20 when Baume degrees between 25-28, water content between 46-50%, general feelings
Energy consumption required for evaporation rate is faster when water content is high under condition is lower, and work is just met when proportion reaches 1.15-1.20
The need for skill, if concentrate raising medicinal extract proportion again there is no need, although improving proportion to stiff paste or clear cream to rear
Continuous technics comparing is good, but time energy consumption is higher.
Wherein, alcohol is preferably alcohol in alcohol precipitation, in order to further improve the fractional dose of neohesperidin and aurantiin, alcohol precipitation
Temperature is not less than 55 DEG C, more preferably preferably 55 DEG C -65 DEG C, 60 DEG C；In order to improve the effect of alcohol precipitation, the concentration of alcohol is preferred
80% is not less than, the consumption of alcohol is not less than 5 times of the medicinal extract after concentration.
Wherein, ethanol herein and alcohol are equivalent.
Wherein, in order to improve filter effect, quickening filtration time and prevent from going mouldy, using plate press filtration wide or using at a high speed
Centrifugal separation comes separating filtrate and sediment.Preferably plate press filtration wide.
Wherein, in order that sediment dissolving is abundant, usually using 5 times of water dissolves of sediment amount.Decolourizing can be from this
The decolorising agent commonly used in field, such as activated carbon.The present invention describes technical side of the invention in detail using 5% activated carbon for decolorising agent
Case.
In the specific embodiment of the present invention, sediment adds 5% activated carbon decolorizing, mistake with 5 times of water dissolves
Filter, spray drying obtains final product the jelly powder of the content 91%-96.4% of white.
Wherein, the separation method of aurantiin is as follows：
The filtrate is concentrated in vacuo, water-filling is entered in the case where temperature is not less than 70 DEG C and is sunk, supernatant is taken after centrifugation, cooled down
Obtain the sediment containing aurantiin and neohesperidin；
To the alcohol for adding temperature to be not higher than 5 DEG C in the sediment containing aurantiin and neohesperidin, obtained after centrifugation
Clear liquid and thick neohesperidin sediment, will obtain aurantiin after supernatant concentration.
Wherein, in order to shorten concentration time, active component will not be inactivated under lower temperature or lost activity on a small quantity,
Concentration is preferably and is concentrated in vacuo.Wherein, in order to reduce energy consumption, the medicinal extract generally after concentration is more than 1.15, more preferably 1.15-
1.20。
Wherein, in order to be more beneficial for the dissolving of neohesperidin and aurantiin, the heavy temperature of water is preferably more than 70 DEG C, from life
The angle temperature for producing benefit is preferably 80 DEG C.
Wherein, in order that concentration after medicinal extract in insoluble substance can more fully precipitate, preferably use at least 5 times and
Water above.
Wherein, centrifugation is preferably high speed centrifugation and takes supernatant, and the laggard freezer of supernatant natural cooling overnight, is obtained containing new
The sediment of skin glycosides and aurantiin.
Wherein, in order to be able to preferably separate aurantiin and neohesperidin, it is cold alcohol that alcohol is selected.The alcohol
Temperature is preferably not higher than 5 DEG C, more preferably 0-5 DEG C.In cold alcohol, in the entrance alcoholic solution that aurantiin can be easier to, and
Solubility of the neohesperidin in cold alcoholic solution diminishes.
Wherein, in order to improve separating effect, the concentration of the alcohol is preferably not lower than 80%, and the usage amount of alcohol is preferred
It is 5 times of sediment amount.In order to separate fully, usually to the sediment containing neohesperidin and aurantiin with 5 times of sediments
The 80% cold alcohol of amount is sufficiently stirred for 2 hours, and aurantiin enters alcoholic solution, and neohesperidin does not dissolve in cold alcohol, and washing is high
Supernatant and thick neohesperidin sediment are obtained after speed centrifugation.
In order to wash fully, sediment obtained above is measured into 80% cold ethanol wash with 2 times for the second time, high speed centrifugation is obtained
To supernatant and neohesperidin sediment.To obtain sediment third time with 1 times measure 80% cold ethanol wash, it is isolated on
Clear liquid and neohesperidin sediment.
One of the invention preferred embodiment in, merge centrifugation after supernatant, after recovered alcohol concentrate drying
Can obtain the aurantiin of light yellow 92.3%-92.6%.
One of the invention preferred embodiment in, the separation method of neohesperidin is as follows：
To alkaline solution is added in the thick neohesperidin sediment, it is sufficiently mixed, filtrate is taken after filtering, then filtrate is adjusted
To acid, collect and precipitate and recrystallize, obtain neohesperidin.
Wherein, neohesperidin is a kind of acidulous material with phenolic hydroxyl group, can be dissolved in alkaline solution, molten in acidity
Can be precipitated out in liquid, according to this property, the purpose that removal of impurities is isolated and purified be reached by the way that alkali soluble acid is heavy.
Wherein, in order to be able to make neohesperidin more fully dissolve, the pH value preferably 10- of solution is made after adding alkaline solution
12, more preferably 11.In addition, in order that new orange peel is cmpletely precipitated, the pH value of acid filtrate is preferably 2-5, more preferably
4。
Wherein, in order to accelerate dissolving, alkaline solution is preferably sodium hydroxide solution.The alkaline solution being usually added into is 5 times
Sediment amount.In addition, in order to further speed up dissolving, can properly increase temperature, in the process, temperature cannot be below
5℃。
Wherein, the solvent preferably ethanol for using is recrystallized.The temperature of ethanol is preferably 60 DEG C.In order to improve dissolving-weight
Crystallization effect, the concentration of ethanol is preferably not less than 80%, more preferably 80%.
Re-crystallization step is preferably：Precipitation after being crystallized under sour environment was dissolved with 80%, 60 DEG C of ethanol solution
Filter cools down recrystallization again, collects the neohesperidin that crystallizing and drying can obtain 98.5%-98.7%.
In the inventive solutions, the water in all steps is preferably pure water, ethanol, hydrochloric acid, NaOH, saturation
Limewash is both preferably the pure or food grade of analysis.
Following examples are used to illustrate the present invention, but are not limited to the scope of the present invention.
Embodiment 1:
1) 500 kilograms of the dried immature fruit of citron orange (RP-HPLC method analysis aurantiin 7.72%, aurantiamarin 0.93%, new orange are taken
Skin glycosides 8.61%, AAS pectin content 10.3%), it is crushed to 100% and crosses 14 mesh sieves；
2) warm water ultrasonic-leaching：500 kilograms of dried immature fruit of citron orange powder put into extractor, extract for the first time, and extractor adds 5000 public affairs
Jin purified water, is heated up to 60 degree and keeps stabilization, opens ultrasonic oscillation, extracts 6 hours, and second extraction adds purified water 2500
Kilogram, 60 degree are heated up to, extract 4 hours, merge with second leaching liquor obtain 6992 kilograms of leaching liquor, filter residue 991 for the first time
Kilogram；
3) isolated and purified to merging extract solution：
A) concentrate：In vacuum degree negative pressure -0.08--0.09MPA, extraction amalgamation liquid is concentrated in vacuo, temperature does not surpass
60 degree are crossed, proportion 1.15-1.20 is concentrated into, 570 kilograms of medicinal extract is obtained；
B) alcohol precipitation：570 kilograms of medicinal extract, 3000 kilograms of 80% alcohol is sufficiently stirred for, and is heated to 60 degree, incubated overnight；
C) filter：Plate press filtration wide obtains 3239 kilograms of filtrates and 320 kilograms of sediments；
D) filtrate concentrates again：3239 kilograms of filter vacuums are concentrated into the concentrated extract of proportion 1.15-1.20, vacuum is adopted
With negative pressure-0.08-0.09MPA, 435 kilograms of medicinal extract is obtained；
E) water sinks：To 435 kilograms of concentrated extracts of previous step with 2200 kilograms of pure water, it is heated to 80 degree and is sufficiently stirred for；
F) it is centrifuged at a high speed：High speed centrifugation is carried out to upper step, temperature must not be less than 70 degree during centrifugation, obtain supernatant 2370
Kilogram and centrifugal sediment, abandon precipitation, the laggard freezer of supernatant natural cooling overnight, obtains being obtained containing neohesperidin and aurantiin
138 kilograms of sediment；
G) ethanol wash：To obtaining 138 kilograms of sediment, 700 kilograms of 80% cold alcohol containing neohesperidin and aurantiin
It is sufficiently stirred for 2 hours, aurantiin enters alcoholic solution, neohesperidin does not dissolve in cold alcohol, supernatant is obtained after washing high speed centrifugation
62 kilograms of 760 kilograms of liquid and thick neohesperidin sediment, 62 kilograms of sediments, second cold ethanol wash of use 120 kg 80%,
High speed centrifugation obtains 51 kilograms of 131 kilograms of supernatant and neohesperidin sediment, and 50 kilograms of alcohol third times wash to obtain supernatant 53
Kilogram and neohesperidin precipitate 47.6 kilograms, merge 944 kilograms of supernatant after three centrifugations, after recovered alcohol concentrate drying
To light yellow 92.6% 35.77 kilograms of aurantiin；
H) isolate and purify：47.6 kilograms of neohesperidin sediments are adjusted with 250 kilograms of pure water and sodium hydroxide solution and meet PH extremely
11 filter precipitation collects filtrates, then obtains the 40.35 kg whites new orange peel of crystallization with the hydrochloric acid regulation collection crystalline deposits of PH to 4.0
Glycosides, the crystallization ethanol dissolution filter of 80% temperature 60 cools down recrystallization again, collects the white needles that crystallizing and drying obtains 98.7%
Neohesperidin crystallizes 36.55 kilograms.
I) pectin is separated：To c) filtering：Plate press filtration wide obtains 3230 kilograms of filtrates and 320 kilograms of sediments, 320 kilograms of precipitations
Thing adds 5% activated carbon decolorizing with 1600 kilograms of water dissolves, and filtering, vacuum spray drying obtains final product the pectin of the content 96.2% of white
48.76 kilograms of powder；
4) aurantiamarin is isolated and purified：To 991 kilograms of filter residue after warm water ultrasonic-leaching again with 5000 kilograms of saturation stone
Buck is extracted 3 hours, 5120 kilograms of filtrate is obtained after filtering and adjusts PH to 4.0 with concentrated hydrochloric acid, and refrigerated overnight precipitates to obtain sediment 126
Kilogram, 126 kilograms of sediments adjust the solution of PH11.0 with 600 kilograms of water sodium hydroxides again, and 625 kilograms of filtrate is obtained after filtering,
Filtrate adjusts the cool overnights of PH to 4.0 with hydrochloric acid, and centrifugation obtains 4.17 kilograms of sediment, by sediment pure water, drying
Obtain 98.2% and obtain 4.07 kilograms of aurantiamarin white, needle-shaped crystals.
Embodiment 2
1) 500 kilograms of the dried immature fruit of citron orange (RP-HPLC method analysis aurantiin 7.64%, aurantiamarin 0.88%, new orange are taken
Skin glycosides 8.33%, AAS pectin content 10.1%), it is crushed to 100% and crosses 14 mesh sieves；
2) warm water ultrasonic-leaching：500 kilograms of dried immature fruit of citron orange powder put into extractor, extract for the first time, and extractor adds 5000 public affairs
Jin purified water, is heated up to 60 degree and keeps stabilization, opens ultrasonic oscillation, extracts 6 hours, and second extraction adds purified water 2500
Kilogram, 60 degree are heated up to, extract 4 hours, merge with second leaching liquor obtain 7039 kilograms of leaching liquor, filter residue 951 for the first time
Kilogram；
3) isolated and purified to merging extract solution：
A) concentrate：In vacuum degree negative pressure -0.08--0.09MPA, extraction amalgamation liquid is concentrated in vacuo, temperature does not surpass
60 degree are crossed, proportion 1.15-1.20 is concentrated into, 551 kilograms of medicinal extract is obtained；
B) alcohol precipitation：551 kilograms of medicinal extract, 3000 kilograms of 80% alcohol is sufficiently stirred for, and is heated to 60 degree, incubated overnight；
C) filter：Plate press filtration wide obtains 3227 kilograms of filtrates and 316 kilograms of sediments；
D) filtrate concentrates again：3227 kilograms of filter vacuums are concentrated into the concentrated extract of proportion 1.15-1.20, vacuum is adopted
With negative pressure-0.08-0.09MPA, 426 kilograms of medicinal extract is obtained；
E) water sinks：To 426 kilograms of concentrated extracts of previous step with 2050 kilograms of pure water, it is heated to 80 degree and is sufficiently stirred for；
F) it is centrifuged at a high speed：High speed centrifugation is carried out to upper step, temperature must not be less than 70 degree during centrifugation, obtain supernatant 2290
Kilogram and centrifugal sediment, abandon precipitation, the laggard freezer of supernatant natural cooling overnight, obtains being obtained containing neohesperidin and aurantiin
132 kilograms of sediment；
G) ethanol wash：To obtaining 132 kilograms of sediment, 650 kilograms of 80% cold alcohol containing neohesperidin and aurantiin
It is sufficiently stirred for 2 hours, aurantiin enters alcoholic solution, neohesperidin does not dissolve in cold alcohol, supernatant is obtained after washing high speed centrifugation
58 kilograms of 717 kilograms of liquid and thick neohesperidin sediment, 58 kilograms of sediments, second cold ethanol wash of use 120 kg 80%,
High speed centrifugation obtains 49 kilograms of 128 kilograms of supernatant and neohesperidin sediment, and 50 kilograms of alcohol third times wash to obtain supernatant 52
Kilogram and neohesperidin precipitate 46.5 kilograms, merge 897 kilograms of supernatant after three centrifugations, after recovered alcohol concentrate drying
To light yellow 92.3% 34.6 kilograms of aurantiin；
H) isolate and purify：46.5 kilograms of neohesperidin sediments are adjusted with 240 kilograms of pure water and sodium hydroxide solution and meet PH extremely
11 filter precipitation collects filtrates, then obtains the 40.11 kg whites new orange peel of crystallization with the hydrochloric acid regulation collection crystalline deposits of PH to 4.0
Glycosides, the crystallization ethanol dissolution filter of 80% temperature 60 cools down recrystallization again, collects the white needles that crystallizing and drying obtains 98.5%
Neohesperidin crystallizes 34.79 kilograms.
I) pectin is separated：To c) filtering：Plate press filtration wide obtains 3190 kilograms of filtrates and 316 kilograms of sediments, 316 kilograms of precipitations
Thing adds 5% activated carbon decolorizing with 1600 kilograms of water dissolves, and filtering, vacuum spray drying obtains final product the pectin of the content 96.4% of white
47.87 kilograms of powder；
4) aurantiamarin is isolated and purified：To 951 kilograms of filter residue after warm water ultrasonic-leaching again with 4800 kilograms of saturation stone
Buck is extracted 3 hours, 5050 kilograms of filtrate is obtained after filtering and adjusts PH to 4.0 with concentrated hydrochloric acid, and refrigerated overnight precipitates to obtain sediment 117
Kilogram, 117 kilograms of sediments adjust the solution of PH11.0 with 600 kilograms of water sodium hydroxides again, and 631 kilograms of filtrate is obtained after filtering,
Filtrate adjusts the cool overnights of PH to 4.0 with hydrochloric acid, and centrifugation obtains 4.13 kilograms of sediment, by sediment pure water, drying
Obtain 98.3% and obtain 3.85 kilograms of aurantiamarin white, needle-shaped crystals.
Embodiment 3:
1) 500 kilograms of the dried immature fruit of citron orange (RP-HPLC method analysis aurantiin 7.81%, aurantiamarin 0.86%, new orange are taken
Skin glycosides 8.72%, AAS pectin content 9.7%), it is crushed to 100% and crosses 14 mesh sieves；
2) warm water ultrasonic-leaching：500 kilograms of dried immature fruit of citron orange powder put into extractor, extract for the first time, and extractor adds 5000 public affairs
Jin purified water, is heated up to 60 degree and keeps stabilization, opens ultrasonic oscillation, extracts 6 hours, and second extraction adds purified water 2500
Kilogram, 60 degree are heated up to, extract 4 hours, merge with second leaching liquor obtain 7013 kilograms of leaching liquor, filter residue 980 for the first time
Kilogram；
3) isolated and purified to merging extract solution：
A) concentrate：In vacuum degree negative pressure -0.08--0.09MPA, extraction amalgamation liquid is concentrated in vacuo, temperature does not surpass
60 degree are crossed, proportion 1.15-1.20 is concentrated into, 573 kilograms of medicinal extract is obtained；
B) alcohol precipitation：573 kilograms of medicinal extract, 3000 kilograms of 80% alcohol is sufficiently stirred for, and is heated to 60 degree, incubated overnight；
C) filter：Plate press filtration wide obtains 3219 kilograms of filtrates and 331 kilograms of sediments；
D) filtrate concentrates again：3219 kilograms of filter vacuums are concentrated into the concentrated extract of proportion 1.15-1.20, vacuum is adopted
With negative pressure-0.08-0.09MPA, 435 kilograms of medicinal extract is obtained；
E) water sinks：To 435 kilograms of concentrated extracts of previous step with 2200 kilograms of pure water, it is heated to 80 degree and is sufficiently stirred for；
F) it is centrifuged at a high speed：High speed centrifugation is carried out to upper step, temperature must not be less than 70 degree during centrifugation, obtain supernatant 2427
Kilogram and centrifugal sediment, abandon precipitation, the laggard freezer of supernatant natural cooling overnight, obtains being obtained containing neohesperidin and aurantiin
143 kilograms of sediment；
G) ethanol wash：To obtaining 143 kilograms of sediment, 720 kilograms of 80% cold alcohol containing neohesperidin and aurantiin
It is sufficiently stirred for 2 hours, aurantiin enters alcoholic solution, neohesperidin does not dissolve in cold alcohol, supernatant is obtained after washing high speed centrifugation
67.7 kilograms of 793 kilograms of liquid and thick neohesperidin sediment, 67.7 kilograms of sediments are washed for second with 140 kilogram of 80% cold alcohol
Wash, high speed centrifugation obtains 147 kilograms of supernatant and 58.9 kilograms of neohesperidin sediment, 60 kilograms of alcohol third times wash to obtain supernatant
60.8 kilograms of liquid and neohesperidin precipitate 54.7 kilograms, merge 1000.8 kilograms of supernatant after three centrifugations, and recovered alcohol is dense
Contracting obtains light yellow 92.6% 37.26 kilograms of aurantiin after drying；
H) isolate and purify：54.7 kilograms of neohesperidin sediments are adjusted with 280 kilograms of pure water and sodium hydroxide solution and meet PH extremely
11 filter precipitation collects filtrates, then obtains the 43.16 kg whites new orange peel of crystallization with the hydrochloric acid regulation collection crystalline deposits of PH to 4.0
Glycosides, the crystallization ethanol dissolution filter of 80% temperature 60 cools down recrystallization again, collects the white needles that crystallizing and drying obtains 98.6%
Neohesperidin crystallizes 37.57 kilograms.
I) pectin is separated：To c) filtering：Plate press filtration wide obtains 3219 kilograms of filtrates and 331 kilograms of sediments, 331 kilograms of precipitations
Thing adds 5% activated carbon decolorizing with 1650 kilograms of water dissolves, and filtering, vacuum spray drying obtains final product the pectin of the content 96.2% of white
46.55 kilograms of powder；
4) aurantiamarin is isolated and purified：To 980 kilograms of filter residue after warm water ultrasonic-leaching again with 5000 kilograms of saturation stone
Buck is extracted 3 hours, 5111 kilograms of filtrate is obtained after filtering and adjusts PH to 4.0 with concentrated hydrochloric acid, and refrigerated overnight precipitates to obtain sediment 121
Kilogram, 121 kilograms of sediments adjust the solution of PH11.0 with 600 kilograms of water sodium hydroxides again, and 619 kilograms of filtrate is obtained after filtering,
Filtrate adjusts the cool overnights of PH to 4.0 with hydrochloric acid, and centrifugation obtains 3.97 kilograms of sediment, by sediment pure water, drying
Obtain 98.2% and obtain 3.76 kilograms of aurantiamarin white, needle-shaped crystals.
Comparative example 1：
This control methods mainly includes using using the method for separating and purifying high-purity neohesperidin in Fructus Aurantii flavones crude extract
Water and ethanol extract Fructus Aurantii extract from Fructus Aurantii, and Fructus Aurantii flavonoids crude extract is obtained with macroporous resin column chromatography method, use positive fourth
Alcohol is extracted and solvent recrystallization method purifies the neohesperidin for preparing high-purity.
Specific implementation：(this dried immature fruit of citron orange purchases Jiangxi to 500 kilograms of dried immature fruit of citron oranges, through reverse efficient liquid phase chromatographic analysis neohesperidin
Content 8.43%) broken rear 5000 kilogram 80% of first time alcoholic extraction 3 hours, second is small with 2500 kilograms of alcoholic extractions 2
When, macroreticular resin D101 is adsorbed and is afforded 132.6 kilograms of dried immature fruit of citron orange chromocor extract meal, then with n-butanol and spirit solvent
Recrystallization method isolates and purifies 37.97 kilograms of neohesperidin for obtaining 98.5%.
Neohesperidin, aurantiamarin, aurantiin, pectin content detection
1st, the method for rp-hplc determination neohesperidin, aurantiamarin, naringin content, specially：Using
Promosil C 18 (250mm × 4.6mm, 5 μm) chromatographic column, mobile phase is acetonitrile-water (22：78), flow velocity is 1.0mL
Min-1, Detection wavelength 283nm, column temperature are 25 DEG C.
2nd, the method for spectrophotometry pectin content：The measure NY/T2016- of pectin content in fruit and its product
2011 People's Republic of China's agricultural industry criterias
3rd, the results are shown in Table 1：
Table 1:Neohesperidin, aurantiamarin, aurantiin, pectin content and the rate of recovery
The result of table 1 shows：The neohesperidin purity for comparing this method embodiment 1-3 offers with comparative example does not have significance difference
Not, the rate of recovery is slightly lower than the difference of comparative example 5-6%, it is contemplated that the method that comparative example is used is complicated, and organic solvent is to implement
2 times of example, and comparative example has used macroreticular resin, and macroreticular resin environmental pollution and maintenance cost are all very high, so comprehensive
Beneficial to promoting, economy is significantly better than comparative example to analysis this method.
Although above having used general explanation, specific embodiment and experiment, the present invention is made to retouch in detail
State, but on the basis of the present invention, it can be made some modifications or improvements, this is to those skilled in the art apparent
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Scope.
Claims (10)
1. a kind of method to dried immature fruit of citron orange comprehensive utilization, methods described includes：
1) dried immature fruit of citron orange is crushed, is sieved；
2) temperature in use is extracted for 55-60 DEG C of water to the material after sieving, and leaching liquor and filter residue are collected respectively；
3) filter residue purify obtaining aurantiamarin；
And/or, the leaching liquor is separated, obtain one or more in jelly powder, aurantiin, neohesperidin.
2. method according to claim 1, it is characterised in that
Step 1) it is described sieving be 14 mesh sieves.
3. method according to claim 1 and 2, it is characterised in that
The step 2) in extracting times be 2-3 times, total consumption of the water is preferably 12-16 times of raw material survival dose；
And/or, the time of the extraction is 4-6 hours；
More preferably step 2) in extracting times be 2 times：The consumption of extraction water is 8-10 times of bulk drug for the first time, is extracted for the second time
The consumption of water is 4-6 times of bulk drug.
4. the method according to any one of claim 1-3, it is characterised in that the method for purification of the aurantiamarin is as follows：
Filter residue saturated limewater is dissolved, supernatant is taken and is adjusted to acidity, cooling takes precipitation, removal of impurities, after drying
Obtain aurantiamarin.
5. method according to claim 4, it is characterised in that the removal of impurities includes dissolving precipitation alkali lye, mistake
Filtrate is adjusted to acidity after filter, is obtained final product after cool overnight；More preferably by the alkali lye dissolving that the precipitation pH value is 10-12, mistake
Filtrate is adjusted to pH value for 2-5 after filter.
6. the method according to any one of claim 1-5, it is characterised in that the separation method of the jelly powder is as follows：
The leaching liquor is concentrated in vacuo, alcohol precipitation, separating filtrate and sediment are carried out in the case where temperature is not less than 55 DEG C, by institute
Sediment water dissolves are stated, is decolourized, filtering, spray drying obtains final product jelly powder.
7. method according to claim 6, it is characterised in that
Vacuum is -0.08--0.09MPA in the vacuum concentration, and temperature is 55-60 DEG C, and the proportion of concentration is not less than 1.15；
And/or, alcohol is not less than 80% alcohol for concentration in the alcohol precipitation, the consumption of alcohol for 5 times of concentrated extract and more than.
8. the method according to claim 6 or 7, it is characterised in that the separation method of the aurantiin and/or neohesperidin
It is as follows：
The filtrate is concentrated in vacuo, water-filling is entered in the case where temperature is not less than 70 DEG C and is sunk, supernatant is taken after centrifugation, cooling is obtained
Sediment containing aurantiin and neohesperidin；
To the alcohol for adding temperature to be not higher than 5 DEG C in the sediment containing aurantiin and neohesperidin, supernatant is obtained after centrifugation
With thick neohesperidin sediment, aurantiin will be obtained after supernatant concentration；
And/or, the separation method of the neohesperidin is as follows：
To alkaline solution is added in the thick neohesperidin sediment, it is sufficiently mixed, filtrate is taken after filtering, then filtrate is adjusted to acid
Property, collect and precipitate and recrystallize, obtain neohesperidin.
9. method according to claim 8, it is characterised in that
Vacuum is -0.08--0.09MPA in the vacuum concentration, and temperature is 55-60 DEG C, and the proportion of concentration is not less than 1.15；
And/or, the heavy temperature of preferably described water is 70-80 DEG C；
And/or, the temperature of preferably described alcohol is 0-5 DEG C, and the concentration of alcohol is not less than 80%；
And/or, the pH value of alkaline solution is 10-12, and the pH value of acid filtrate is 2-5；
And/or, the solvent of recrystallization is not less than 80% ethanol for concentration, and the temperature of ethanol is not less than 60 DEG C.
10. a kind of method that neohesperidin is extracted from the dried immature fruit of citron orange, methods described includes：
The dried immature fruit of citron orange is crushed, is sieved；
Temperature in use is extracted for 55-60 DEG C of water to the material after sieving, and leaching liquor and filter residue are collected respectively；
The leaching liquor is concentrated in vacuo, alcohol precipitation, separating filtrate and sediment are carried out in the case where temperature is not less than 55 DEG C；
The filtrate is concentrated in vacuo, water-filling is entered in the case where temperature is not less than 70 DEG C and is sunk, supernatant is taken after centrifugation, cooling is obtained
Sediment containing aurantiin and neohesperidin；
To temperature is added in the sediment containing aurantiin and neohesperidin for 0-5 DEG C of alcohol, obtained after centrifugation supernatant and
Thick neohesperidin sediment；
To alkaline solution is added in the thick neohesperidin sediment, it is sufficiently mixed, filtrate is taken after filtering, then filtrate is adjusted to acid
Property, collect and precipitate and recrystallize, obtain neohesperidin.
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| CN108822169A (en) * | 2018-09-18 | 2018-11-16 | 湘西华方制药有限公司 | The heavy aurantiamarin that alcohol extracting prepares the method for crystallising of heavy aurantiamarin and is prepared |
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| CN108299520A (en) * | 2018-05-03 | 2018-07-20 | 中南民族大学 | Promote the method and aurantiamarin of extraction aurantiamarin purity |
| CN108822169A (en) * | 2018-09-18 | 2018-11-16 | 湘西华方制药有限公司 | The heavy aurantiamarin that alcohol extracting prepares the method for crystallising of heavy aurantiamarin and is prepared |
| CN111393310A (en) * | 2020-04-24 | 2020-07-10 | 永州华茂生物科技有限责任公司 | Extraction method of immature bitter orange extract |
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| CN111732622B (en) * | 2020-07-08 | 2021-11-23 | 湖南华诚生物资源股份有限公司 | Method for extracting hesperidin from immature bitter orange |
| CN111777653A (en) * | 2020-08-21 | 2020-10-16 | 江西海富生物工程有限公司 | Preparation method of pure natural high-content neohesperidin |
| CN111777653B (en) * | 2020-08-21 | 2023-07-21 | 江西海富生物工程有限公司 | Preparation method of pure natural high-content neohesperidin |
| CN112047846A (en) * | 2020-10-13 | 2020-12-08 | 四川大学 | Method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using ultrasonic-assisted aqueous two-phase system |
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